ethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-isobenzofuran-5-yl)-4-methylhex-4-enoate
mycophenolic acid
Conditions | Yield |
---|---|
With lithium hydroxide In methanol for 12h; | 98% |
With lithium hydroxide In methanol at 23℃; for 5h; | 93% |
With lithium hydroxide In methanol; water at 25℃; for 1h; | 71% |
methyl mycophenolate
mycophenolic acid
Conditions | Yield |
---|---|
With lithium hydroxide monohydrate In tetrahydrofuran; water at 25℃; for 24h; | 96% |
With lithium hydroxide In tetrahydrofuran for 3h; Ambient temperature; | 85% |
With water; lithium hydroxide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; | 66% |
7-hydroxy-6-[(E)-6-hydroxy-3-methylhex-2-enyl]-5-methoxy-4-methyl-3H-2-benzofuran-1-one
mycophenolic acid
Conditions | Yield |
---|---|
With jones reagent In acetone at -30℃; for 5h; | 61% |
D-glucose
mycophenolic acid
Conditions | Yield |
---|---|
With manganese(II) sulfate; potassium permanganate; potassium dihydrogenphosphate; L-methionine; Penicillium brevicompactum No. 4-23-11 spores; magnesium sulfate; copper(II) sulfate; iron(II) sulfate; glycine; zinc(II) sulfate In water at 26℃; for 360h; Product distribution; effect of the spore concentration, effect of addition of various adsorbents; | |
With manganese(II) sulfate; potassium permanganate; potassium dihydrogenphosphate; L-methionine; Celite; Penicillium brevicompactum No. 4-23-11 spores; magnesium sulfate; copper(II) sulfate; iron(II) sulfate; glycine; zinc(II) sulfate In water at 26℃; for 360h; Product distribution; various drug-resistant, methionine or glutamate auxotrophic mutants, effect of L-methionine concentration, effect of L-glutamate concentration; |
7-O-Methylmycophenolic acid
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 189 mg / ethyl acetate 2: BCl3 / CH2Cl2 / 12 h / 20 °C 3: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: ethyl acetate 2: 86 percent / BCl3 / CH2Cl2 / 192 h 3: LiOH / H2O View Scheme |
5,7-dimethoxy-6-(5-methoxycarbonyl-3-methyl-2-pentenyl)-4-methylphthalide
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: BCl3 / CH2Cl2 / 12 h / 20 °C 2: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 86 percent / BCl3 / CH2Cl2 / 192 h 2: LiOH / H2O View Scheme |
(E)-6-(4,6-Dimethoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-4-methyl-hex-4-enal
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: Jones reagent / acetone / 4 h / -30 °C 2: 189 mg / ethyl acetate 3: BCl3 / CH2Cl2 / 12 h / 20 °C 4: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: CrO3, acid / acetone / -30 °C 2: ethyl acetate 3: 86 percent / BCl3 / CH2Cl2 / 192 h 4: LiOH / H2O View Scheme |
6-((E)-3,7-Dimethyl-octa-2,6-dienyl)-5,7-dimethoxy-4-methyl-3H-isobenzofuran-1-one
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: O3 / methanol / -78 °C 1.2: Me2S / methanol / 3 h / -10 - 20 °C 2.1: Jones reagent / acetone / 4 h / -30 °C 3.1: 189 mg / ethyl acetate 4.1: BCl3 / CH2Cl2 / 12 h / 20 °C 5.1: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1: 75.4 percent / NaOAc; m-CPBA / CH2Cl2 / 7 h / -70 °C 2: HIO4*2H2O / diethyl ether; tetrahydrofuran / 1 h / 0 °C 3: Jones reagent / acetone / 4 h / -30 °C 4: 189 mg / ethyl acetate 5: BCl3 / CH2Cl2 / 12 h / 20 °C 6: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: O3, Me2S / CH2Cl2; pyridine / -78 °C 2: CrO3, acid / acetone / -30 °C 3: ethyl acetate 4: 86 percent / BCl3 / CH2Cl2 / 192 h 5: LiOH / H2O View Scheme |
3-((E)-3,7-Dimethyl-octa-2,6-dienyl)-6-(2,2-dimethyl-propionyloxymethyl)-2,4-dimethoxy-5-methyl-benzoic acid methyl ester
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 100 percent / K2CO3 / methanol / 6 h 2.1: O3 / methanol / -78 °C 2.2: Me2S / methanol / 3 h / -10 - 20 °C 3.1: Jones reagent / acetone / 4 h / -30 °C 4.1: 189 mg / ethyl acetate 5.1: BCl3 / CH2Cl2 / 12 h / 20 °C 6.1: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1: 100 percent / K2CO3 / methanol / 6 h 2: 75.4 percent / NaOAc; m-CPBA / CH2Cl2 / 7 h / -70 °C 3: HIO4*2H2O / diethyl ether; tetrahydrofuran / 1 h / 0 °C 4: Jones reagent / acetone / 4 h / -30 °C 5: 189 mg / ethyl acetate 6: BCl3 / CH2Cl2 / 12 h / 20 °C 7: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1: K2CO3 / methanol 2: O3, Me2S / CH2Cl2; pyridine / -78 °C 3: CrO3, acid / acetone / -30 °C 4: ethyl acetate 5: 86 percent / BCl3 / CH2Cl2 / 192 h 6: LiOH / H2O View Scheme |
3-((E)-3,7-Dimethyl-octa-2,6-dienyl)-6-(2,2-dimethyl-propionyloxymethyl)-5-formyl-2,4-dimethoxy-benzoic acid methyl ester
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: 89 percent / NaBH4 / methanol / 0.5 h 2.1: Et3N / CH2Cl2 / 2.5 h / 25 °C 3.1: 372 mg / NaBH4 / dimethylformamide / 2.5 h / 25 °C 4.1: 100 percent / K2CO3 / methanol / 6 h 5.1: O3 / methanol / -78 °C 5.2: Me2S / methanol / 3 h / -10 - 20 °C 6.1: Jones reagent / acetone / 4 h / -30 °C 7.1: 189 mg / ethyl acetate 8.1: BCl3 / CH2Cl2 / 12 h / 20 °C 9.1: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 10 steps 1: 89 percent / NaBH4 / methanol / 0.5 h 2: Et3N / CH2Cl2 / 2.5 h / 25 °C 3: 372 mg / NaBH4 / dimethylformamide / 2.5 h / 25 °C 4: 100 percent / K2CO3 / methanol / 6 h 5: 75.4 percent / NaOAc; m-CPBA / CH2Cl2 / 7 h / -70 °C 6: HIO4*2H2O / diethyl ether; tetrahydrofuran / 1 h / 0 °C 7: Jones reagent / acetone / 4 h / -30 °C 8: 189 mg / ethyl acetate 9: BCl3 / CH2Cl2 / 12 h / 20 °C 10: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 9 steps 1: 89 percent / NaBH4 / methanol 2: Et3N / CH2Cl2 / 1.5 h 3: NaBH4 / dimethylformamide 4: K2CO3 / methanol 5: O3, Me2S / CH2Cl2; pyridine / -78 °C 6: CrO3, acid / acetone / -30 °C 7: ethyl acetate 8: 86 percent / BCl3 / CH2Cl2 / 192 h 9: LiOH / H2O View Scheme |
3-((E)-3,7-Dimethyl-octa-2,6-dienyl)-6-(2,2-dimethyl-propionyloxymethyl)-5-hydroxymethyl-2,4-dimethoxy-benzoic acid methyl ester
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: Et3N / CH2Cl2 / 2.5 h / 25 °C 2.1: 372 mg / NaBH4 / dimethylformamide / 2.5 h / 25 °C 3.1: 100 percent / K2CO3 / methanol / 6 h 4.1: O3 / methanol / -78 °C 4.2: Me2S / methanol / 3 h / -10 - 20 °C 5.1: Jones reagent / acetone / 4 h / -30 °C 6.1: 189 mg / ethyl acetate 7.1: BCl3 / CH2Cl2 / 12 h / 20 °C 8.1: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 9 steps 1: Et3N / CH2Cl2 / 2.5 h / 25 °C 2: 372 mg / NaBH4 / dimethylformamide / 2.5 h / 25 °C 3: 100 percent / K2CO3 / methanol / 6 h 4: 75.4 percent / NaOAc; m-CPBA / CH2Cl2 / 7 h / -70 °C 5: HIO4*2H2O / diethyl ether; tetrahydrofuran / 1 h / 0 °C 6: Jones reagent / acetone / 4 h / -30 °C 7: 189 mg / ethyl acetate 8: BCl3 / CH2Cl2 / 12 h / 20 °C 9: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1: Et3N / CH2Cl2 / 1.5 h 2: NaBH4 / dimethylformamide 3: K2CO3 / methanol 4: O3, Me2S / CH2Cl2; pyridine / -78 °C 5: CrO3, acid / acetone / -30 °C 6: ethyl acetate 7: 86 percent / BCl3 / CH2Cl2 / 192 h 8: LiOH / H2O View Scheme |
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 372 mg / NaBH4 / dimethylformamide / 2.5 h / 25 °C 2.1: 100 percent / K2CO3 / methanol / 6 h 3.1: O3 / methanol / -78 °C 3.2: Me2S / methanol / 3 h / -10 - 20 °C 4.1: Jones reagent / acetone / 4 h / -30 °C 5.1: 189 mg / ethyl acetate 6.1: BCl3 / CH2Cl2 / 12 h / 20 °C 7.1: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1: 372 mg / NaBH4 / dimethylformamide / 2.5 h / 25 °C 2: 100 percent / K2CO3 / methanol / 6 h 3: 75.4 percent / NaOAc; m-CPBA / CH2Cl2 / 7 h / -70 °C 4: HIO4*2H2O / diethyl ether; tetrahydrofuran / 1 h / 0 °C 5: Jones reagent / acetone / 4 h / -30 °C 6: 189 mg / ethyl acetate 7: BCl3 / CH2Cl2 / 12 h / 20 °C 8: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1: NaBH4 / dimethylformamide 2: K2CO3 / methanol 3: O3, Me2S / CH2Cl2; pyridine / -78 °C 4: CrO3, acid / acetone / -30 °C 5: ethyl acetate 6: 86 percent / BCl3 / CH2Cl2 / 192 h 7: LiOH / H2O View Scheme |
6-[5-(3,3-dimethyl-oxiranyl)-3-methyl-pent-2-enyl]-5,7-dimethoxy-4-methyl-3H-isobenzofuran-1-one
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: HIO4*2H2O / diethyl ether; tetrahydrofuran / 1 h / 0 °C 2: Jones reagent / acetone / 4 h / -30 °C 3: 189 mg / ethyl acetate 4: BCl3 / CH2Cl2 / 12 h / 20 °C 5: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme |
3-((E)-3,7-Dimethyl-octa-2,6-dienyl)-6-(2,2-dimethyl-propionyloxymethyl)-5-formyl-2,4-dihydroxy-benzoic acid methyl ester
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 88 percent / NaH / dimethylformamide 2: 89 percent / NaBH4 / methanol 3: Et3N / CH2Cl2 / 1.5 h 4: NaBH4 / dimethylformamide 5: K2CO3 / methanol 6: O3, Me2S / CH2Cl2; pyridine / -78 °C 7: CrO3, acid / acetone / -30 °C 8: ethyl acetate 9: 86 percent / BCl3 / CH2Cl2 / 192 h 10: LiOH / H2O View Scheme |
(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 86 percent / N,N-diisopropylethylamine / CH2Cl2 / 2 h / Ambient temperature 2: 67 percent / tetrahydrofuran / 0.67 h / -40 °C 3: pivalic acid / xylene / 6 h / 135 - 140 °C 4: PPTS / 2-methyl-propan-2-ol / 6 h / 80 °C 5: 98 percent / aq. LiOH / methanol / 12 h View Scheme |
4-Hydroxy-2-methoxy-5-methyl-3,6-dihydro-2H-benzo[2,1-b;3,4-c']difuran-8-one
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 1.) NaH / 1.) DMF, 0 ged C, 15 min, 2.) DMF, a) 0 deg C, 30 min, b) RT, 30 min 2: 100 percent / 89percent formic acid / 0.33 h / Ambient temperature 3: 86 percent / N,N-diisopropylethylamine / CH2Cl2 / 2 h / Ambient temperature 4: 67 percent / tetrahydrofuran / 0.67 h / -40 °C 5: pivalic acid / xylene / 6 h / 135 - 140 °C 6: PPTS / 2-methyl-propan-2-ol / 6 h / 80 °C 7: 98 percent / aq. LiOH / methanol / 12 h View Scheme |
2,4-Dimethoxy-5-methyl-3,6-dihydro-2H-benzo[2,1-b;3,4-c']difuran-8-one
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 100 percent / 89percent formic acid / 0.33 h / Ambient temperature 2: 86 percent / N,N-diisopropylethylamine / CH2Cl2 / 2 h / Ambient temperature 3: 67 percent / tetrahydrofuran / 0.67 h / -40 °C 4: pivalic acid / xylene / 6 h / 135 - 140 °C 5: PPTS / 2-methyl-propan-2-ol / 6 h / 80 °C 6: 98 percent / aq. LiOH / methanol / 12 h View Scheme |
[6-methoxy-4-(2-methoxyethoxymethoxy)-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl]-acetaldehyde
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 67 percent / tetrahydrofuran / 0.67 h / -40 °C 2: pivalic acid / xylene / 6 h / 135 - 140 °C 3: PPTS / 2-methyl-propan-2-ol / 6 h / 80 °C 4: 98 percent / aq. LiOH / methanol / 12 h View Scheme |
6-(2-hydroxy-3-methylbut-3-enyl)-5-methoxy-7-(2-methoxyethoxymethoxy)-4-methyl-3H-isobenzofuran-2-one
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pivalic acid / xylene / 6 h / 135 - 140 °C 2: PPTS / 2-methyl-propan-2-ol / 6 h / 80 °C 3: 98 percent / aq. LiOH / methanol / 12 h View Scheme |
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: PPTS / 2-methyl-propan-2-ol / 6 h / 80 °C 2: 98 percent / aq. LiOH / methanol / 12 h View Scheme |
7-hydroxy-5-methoxy-4-methylisobenzofuran-1(3H)-one
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 79 percent / benzyl trimethyl ammonium dichloroiodate, NaHCO3 / CH2Cl2; methanol / Ambient temperature 2: 86 percent / iPr2NEt / CH2Cl2 / 1.5 h 3: 53 percent / Pd(dba)2, AsPh3, NMP / 4 h / 100 °C 4: 88 percent / H2SO4 / methanol; tetrahydrofuran / 0.75 h / Ambient temperature 5: 85 percent / LiOH*H2O / tetrahydrofuran / 3 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: N-iodo-succinimide / N,N-dimethyl-formamide / 10 h / 25 °C 2: tetrakis(triphenylphosphine) palladium(0); triphenylphosphine / N,N-dimethyl-formamide / 16 h / 20 - 100 °C / Inert atmosphere 3: lithium hydroxide monohydrate / water; tetrahydrofuran / 24 h / 25 °C View Scheme | |
Multi-step reaction with 3 steps 1: N-iodo-succinimide / N,N-dimethyl-formamide / 10 h / 25 °C 2: triphenylphosphine; palladium diacetate / N,N-dimethyl-formamide / 24 h / 100 °C 3: lithium hydroxide monohydrate / water; tetrahydrofuran / 24 h / 25 °C View Scheme |
7-hydroxy-6-iodo-5-methoxy-4-methylisobenzofuran-1(3H)-one
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 86 percent / iPr2NEt / CH2Cl2 / 1.5 h 2: 53 percent / Pd(dba)2, AsPh3, NMP / 4 h / 100 °C 3: 88 percent / H2SO4 / methanol; tetrahydrofuran / 0.75 h / Ambient temperature 4: 85 percent / LiOH*H2O / tetrahydrofuran / 3 h / Ambient temperature View Scheme |
6-Iodo-5-methoxy-4-methyl-7-(2-trimethylsilanyl-ethoxymethoxy)-3H-isobenzofuran-1-one
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 53 percent / Pd(dba)2, AsPh3, NMP / 4 h / 100 °C 2: 88 percent / H2SO4 / methanol; tetrahydrofuran / 0.75 h / Ambient temperature 3: 85 percent / LiOH*H2O / tetrahydrofuran / 3 h / Ambient temperature View Scheme |
(E)-6-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxymethoxy)-1,3-dihydro-isobenzofuran-5-yl]-4-methyl-hex-4-enoic acid methyl ester
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 88 percent / H2SO4 / methanol; tetrahydrofuran / 0.75 h / Ambient temperature 2: 85 percent / LiOH*H2O / tetrahydrofuran / 3 h / Ambient temperature View Scheme |
Ethyl E-6-<1,3-Dihydro-4-(tert-butyldimethylsilyloxy)-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl>-4-methyl-4-hexenoate
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 98 percent / nBu4NF / tetrahydrofuran / 1 h 2: 93 percent / aq. LiOH / methanol / 5 h / 23 °C View Scheme | |
Multi-step reaction with 2 steps 1: 83 percent / n-Bu4NF / tetrahydrofuran / 0.25 h / 25 °C 2: 71 percent / LiOH / methanol; H2O / 1 h / 25 °C View Scheme |
(E)-6-acetoxy-4-methyl-4-hexenal
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 84 percent / NaBH4 / ethanol / 0.42 h / 25 °C 2: triethylamine / 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / Ambient temperature 3: K2CO3 / methanol / 24 h / Ambient temperature 4: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h 5: 73 percent / benzene / 14 h / 120 °C / in a sealed tube 6: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C 7: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 8: conc. HCl / methanol / 4.5 h / Heating 9: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme |
<(2E)-6-Hydroxy-3-methyl-2-hexenyl>acetat
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: triethylamine / 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / Ambient temperature 2: K2CO3 / methanol / 24 h / Ambient temperature 3: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h 4: 73 percent / benzene / 14 h / 120 °C / in a sealed tube 5: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C 6: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 7: conc. HCl / methanol / 4.5 h / Heating 8: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme |
(E)-6-((tert-butyldimethylsilyl)oxy)-3-methylhex-2-en-1-yl acetate
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: K2CO3 / methanol / 24 h / Ambient temperature 2: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h 3: 73 percent / benzene / 14 h / 120 °C / in a sealed tube 4: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C 5: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 6: conc. HCl / methanol / 4.5 h / Heating 7: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme |
(E)-3-methyl-6-<(tert-butyldimethylsilyl)oxy>-2-hexen-1-ol
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h 2: 73 percent / benzene / 14 h / 120 °C / in a sealed tube 3: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C 4: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 5: conc. HCl / methanol / 4.5 h / Heating 6: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme |
Conditions | Yield |
---|---|
With sulfuric acid for 2h; Heating; | 100% |
With sulfuric acid for 20h; Ambient temperature; | 95% |
With toluene-4-sulfonic acid for 2h; Reflux; | 95.86% |
mycophenolic acid
Conditions | Yield |
---|---|
With sodium methylate In methanol; ethyl acetate at 20℃; for 1h; Product distribution / selectivity; Charcoal; | 97% |
With sodium methylate In methanol; ethyl acetate at 20℃; for 0.5h; Product distribution / selectivity; | 94% |
With sodium methylate In methanol; ISOPROPYLAMIDE at 20℃; for 0.166667h; Product distribution / selectivity; | 92% |
Conditions | Yield |
---|---|
With trimethylbenzylammonium bromide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h; | 96% |
mycophenolic acid
allyl bromide
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 18h; | 93% |
ethanol
mycophenolic acid
ethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-isobenzofuran-5-yl)-4-methylhex-4-enoate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 2h; Reflux; | 92% |
mycophenolic acid
A
7-hydroxy-5-methoxy-4-methyl-6-(2-(2-methyl-5-oxotetrahydrofuran-2-yl)ethyl)isobenzofuran-1(3H)-one
B
mycochromanic acid
Conditions | Yield |
---|---|
With sulfuric acid In acetic acid for 4h; Heating; | A 5% B 90% |
mycophenolic acid
5,7-dimethoxy-6-(5-methoxycarbonyl-3-methyl-2-pentenyl)-4-methylphthalide
Conditions | Yield |
---|---|
In methanol at 20℃; for 12h; | 90% |
lauric anhydride
mycophenolic acid
(E)-6-(1,3-dihydro-4-dodecanoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 120h; | 90% |
mycophenolic acid
tert-butyldimethylsilyl chloride
(E)-6-(4-tert-butyldimethylsilyloxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoic acid
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 1h; Inert atmosphere; | 89% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 88h; | 60% |
Conditions | Yield |
---|---|
Stage #1: 1-hydroxy-pyrrolidine-2,5-dione; mycophenolic acid In acetonitrile Cooling with ice; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile for 24.5h; | 89% |
mycophenolic acid
nor-O-methylmycophenolic acid
Conditions | Yield |
---|---|
With lithium iodide | 88.5% |
With pyridine; 2,3,5-trimethyl-pyridine; lithium iodide at 120℃; for 18h; | 74% |
mycophenolic acid
glycine ethyl ester hydrochloride
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 50h; | 86% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine Inert atmosphere; | 86% |
mycophenolic acid
tert-butylamine
6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid t-butylamine salt
Conditions | Yield |
---|---|
In ethyl acetate at 22 - 60℃; for 1h; Product distribution / selectivity; | 85.6% |
Conditions | Yield |
---|---|
toluene-4-sulfonic acid at 160℃; for 5h; Product distribution / selectivity; | 84% |
(1S)-10-camphorsulfonic acid at 150 - 155℃; for 8h; Product distribution / selectivity; | 84% |
at 160℃; for 5h; Product distribution / selectivity; | 84% |
mycophenolic acid
tert-butyl (2-((2-aminoethyl)(methyl)amino)ethyl)carbamate
(E)-tert-butyl 2-((2-(6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enamido)ethyl)(methyl)amino)ethylcarbamate
Conditions | Yield |
---|---|
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile at 20℃; for 18h; | 84% |
(OC-6-33)-(diammine)dichloridodihydroxidoplatinum(IV)
mycophenolic acid
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 40℃; for 60h; Temperature; Darkness; | 83.9% |
Conditions | Yield |
---|---|
With pyridine; dmap at 0℃; | 83% |
With pyridine; dmap at 20℃; | 62% |
mycophenolic acid
tert-butyl 2-(2-aminoethoxy)ethylcarbamate
(E)-tert-butyl 2-(2-(6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enamido)ethoxy)ethylcarbamate
Conditions | Yield |
---|---|
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile at 20℃; for 18h; | 83% |
mycophenolic acid
3-(5-Carboxy-3-methyl-pent-2t-enyl)-4-hydroxy-6-hydroxymethyl-2-methoxy-toluol; 6-(6-Hydroxy-4-hydroxymethyl-2-methoxy-3-methyl-phenyl)-4-methyl-hex-4t-ensaeure
Conditions | Yield |
---|---|
With lithium hydroxide In water for 96h; Heating; | 82% |
mycophenolic acid
Conditions | Yield |
---|---|
Stage #1: mycophenolic acid; α,β-D-glucuronate With 4-methyl-morpholine In acetonitrile at 20℃; for 2h; Molecular sieve; Inert atmosphere; Stage #2: With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate In acetonitrile at 20℃; for 3h; Inert atmosphere; Molecular sieve; | 82% |
mycophenolic acid
(R)-leucine methyl ester hydrochloride
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 50h; | 81% |
mycophenolic acid
propargyl bromide
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene; acetonitrile at 20℃; for 48h; | 81% |
mycophenolic acid
4-chloro-3-trifluoromethyl-aniline
Conditions | Yield |
---|---|
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 80% |
mycophenolic acid
triethylamine
6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid triethylamine salt
Conditions | Yield |
---|---|
In ethyl acetate at 10 - 60℃; for 1h; Product distribution / selectivity; | 78.7% |
In ethyl acetate for 0.5h; |
mycophenolic acid
D-alanine methyl ester hydrochloride
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 50h; | 77% |
2-(triphenylphosphoranylidene)propionaldehyde
mycophenolic acid
(E)-4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-2-methylbut-2-enal
Conditions | Yield |
---|---|
Stage #1: mycophenolic acid With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; water; acetone at 20℃; for 1.5h; Stage #2: 2-(triphenylphosphoranylidene)propionaldehyde In benzene at 90℃; for 24h; Inert atmosphere; | 77% |
mycophenolic acid
isopropylamine
6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid isopropylamine salt
Conditions | Yield |
---|---|
In ethyl acetate at 11 - 55℃; for 2h; | 75.1% |
Molecular Structure of Mycophenolic acid (CAS NO.24280-93-1):
CAS Number: 24280-93-1
Molecular Formula: C17H20O6
Molecular Weight: 320.37
H bond acceptors: 6
H bond donors: 2
Freely Rotating Bonds: 7
Polar Surface Area: 71.06 Å2
EINECS: 246-119-3
Density: 1.29 g/cm3
Melting Point: 141oC
Boiling Point: 611.6oC at 760 mmHg
Flash Point: 225.8oC
Solubility: Almost insoluble in cold water. Soluble in alcohol
Appearance: White to off-white powder
Properties: Needles from hot water.
Storage temp: 2-8oC
Solubility:methanol: 50 mg/mL, clear, colorless to faintly yellow
Form: powder
Merck: 13,6352
Product Categories: Active Pharmaceutical Ingredients; Aromatics Compounds; Aromatics; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals
InChI
InChI=1/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/b9-4+
Smiles
c12c(c(c(C\C=C(\CCC(O)=O)C)c(c1C)OC)O)C(=O)OC2
1. | dni-mus:lym 200 nmol/L | CNREA8 Cancer Research. 45 (1985),5512. | ||
2. | oms-mus:lym 400 nmol/L | CNREA8 Cancer Research. 45 (1985),5512. | ||
3. | orl-rat LD50:352 mg/kg | TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. 29 (1982),400. | ||
4. | ivn-rat LD50:450 mg/kg | PMDCAY Progress in Medical Chemistry. 9 (1973),1. | ||
5. | ipr-rat LD50:220 mg/kg | TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. 29 (1982),400. | ||
6. | scu-rat LD50:230 mg/kg | TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. 29 (1982),400. | ||
7. | orl-mus LDLo:1000 mg/kg | 85GDA2 CRC Handbook of Antibiotic Compounds, Volumes 1-9. 5 (1981),445. | ||
8. | ipr-mus LD50:505 mg/kg | TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. 29 (1982),400. | ||
9. | ivn-mus LDLo:500 mg/kg | 85ERAY Antibiotics: Origin, Nature, and Properties. 3 (1978),1740. |
EPA Genetic Toxicology Program.
A poison by ingestion and intraperitoneal routes. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety Information of Mycophenolic acid (CAS NO.24280-93-1):
Hazard Codes: Xn
Risk Statements: 22-61-40
R22:Harmful if swallowed.
R61:May cause harm to the unborn child.
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 53-45-36/37
S53:Avoid exposure - obtain special instructions before use.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37:Wear suitable protective clothing and gloves.
RIDADR: 2811
WGK Germany: 3
RTECS: MP8050000
F: 10
HazardClass: 6.1(b)
PackingGroup: III
Mycophenolic acid , with CAS number of 24280-93-1, can be called 6-(1,3-Dihydro-7-hydroxy-5-methoxy-4-methyl-1-oxoisobenzofuran-6-yl)-4-methyl-4-hexanoic acid ; 6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid . It is a white to off-white powder. Mycophenolic acid (CAS NO.24280-93-1) is an antibiotic produced by Penicillium brevi-compactum, P. Stoloniferum and related spp. A selective inhibitor of lymphocyte proliferation by blocking inosine monophosphate dehydrogenase, an enzyme involved in the de novo synthesis of purine nucleot.
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